MiMeDB: Showing metabocard for Dihydroxyacetone phosphate acyl ester (MMDBc0032956)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:28:49 UTC

Update Date

2024-04-30 19:56:17 UTC

Metabolite ID

MMDBc0032956

Metabolite Identification

Common Name

Dihydroxyacetone phosphate acyl ester

Description

Dihydroxyacetone phosphate acyl ester (1-acylglycerone 3-phosphate) is found in the glycerophospholipid metabolism and ether lipid metabolism pathways. In the glycerophospholipid metabolism pathway, 1-acylglycerone 3-phosphate is created from glycerone phosphate, a reaction catalyzed by glyceronephosphate O-acyltransferase [EC:2.3.1.42].

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.881 -10.617   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.111  -9.283   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      20.571  -9.283   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      22.881  -7.950   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      22.111  -6.616   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      22.881  -5.283   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      24.214  -6.053   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      21.547  -4.513   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      23.650  -3.949   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      24.420 -10.617   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      25.190 -11.951   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      26.730 -11.951   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
Dihydroxyacetone phosphoric acid acyl ester	Generator
1-Acyl-glycerone 3-phosphate	HMDB
1-Acylglycerone 3-phosphate	HMDB
1-Acylglycerone 3-phosphates	HMDB
Acylglycerone phosphate	HMDB
[3-(Formyloxy)-2-oxopropoxy]phosphonate	Generator, HMDB

Molecular Formula

C₄H₇O₇P

Average Mass

198.0679

Monoisotopic Mass

197.99293909

IUPAC Name

[3-(formyloxy)-2-oxopropoxy]phosphonic acid

Traditional Name

3-(formyloxy)-2-oxopropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

OP(O)(=O)OCC(=O)COC=O

InChI Identifier

InChI=1S/C4H7O7P/c5-3-10-1-4(6)2-11-12(7,8)9/h3H,1-2H2,(H2,7,8,9)

InChI Key

IWFZHMQFZRLGDQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

O-acylglycerone-phosphates

Alternative Parents

Substituents

O-acylglycerone-phosphate
Monosaccharide phosphate
Alpha-acyloxy ketone
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Monosaccharide
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	14 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	35.13 m³·mol⁻¹	ChemAxon
Polarizability	14.72 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-9400000000-a4c629b2425c0a3d5261	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-bb19454b2c14cffa3566	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001s-3900000000-5db91e654ecce58c783f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p6-9400000000-2f718dd8682c4d2a9d2a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-4900000000-8b1348546e57144d285a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-828668cbcb574c69b008	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-1ab49b82139665921c4b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1900000000-4351f40f807cf7fe2fbc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-9700000000-da29d6bc2198dae0dca8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-31ddf570fb180659d827	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-9700000000-999ce69e965fa50aba96	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-b4d7fda62150ac79ba0d	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193098	Dihydroxyacetone phosphate acyltransferase	Enzyme	O15228	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004397	Dihydroxyacetone phosphate acyl ester	1-oleyl-2-lyso-phosphatidate	aldo-keto reductase family 1, member A1 (aldehyde reductase)		VMH	7669785

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0011750

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028422

KNApSAcK ID

Not Available

Chemspider ID

5256726

KEGG Compound ID

C03372

BioCyc ID

1-ACYL-GLYCERONE-3-PHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6857386

PDB ID

Not Available

ChEBI ID

15835

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Barski OA, Gabbay KH, Grimshaw CE, Bohren KM: Mechanism of human aldehyde reductase: characterization of the active site pocket. Biochemistry. 1995 Sep 5;34(35):11264-75. doi: 10.1021/bi00035a036. [PubMed:7669785 ]

Showing metabocard for Dihydroxyacetone phosphate acyl ester (MMDBc0032956)

MOL for #<Metabolite:0x00007fecdc0254d8>

3D MOL for #<Metabolite:0x00007fecdc0254d8>

3D SDF for #<Metabolite:0x00007fecdc0254d8>

3D-SDF for #<Metabolite:0x00007fecdc0254d8>

PDB for #<Metabolite:0x00007fecdc0254d8>

3D PDB for #<Metabolite:0x00007fecdc0254d8>

SMILES for #<Metabolite:0x00007fecdc0254d8>

INCHI for #<Metabolite:0x00007fecdc0254d8>

Structure for #<Metabolite:0x00007fecdc0254d8>

3D Structure for #<Metabolite:0x00007fecdc0254d8>